1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

Dingben Chen; Ling Huang; Mingyu Liang; Xiaojing Chen; Dongdong Cao; Pan Xiao; Chuanfa Ni; Jinbo Hu

doi:10.3390/molecules29122905

1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me₃SiCF₂H/Me₃SiCF₃ Facilitated by CsF/18-Crown-6

Molecules. 2024 Jun 19;29(12):2905. doi: 10.3390/molecules29122905.

Authors

Dingben Chen^{1

2}, Ling Huang¹, Mingyu Liang¹, Xiaojing Chen¹, Dongdong Cao¹, Pan Xiao^{2

3}, Chuanfa Ni², Jinbo Hu^{2

3}

Affiliations

¹ School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China.
² Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
³ School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China.

Abstract

The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me₃SiRf (Rf = CF₂H, CF₃, CF₂CF₃, CF₂COOEt, and CF₂SPh) under mild conditions are described. Although Me₃SiCF₂H shows lower reactivity than Me₃SiCF₃, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes.

Keywords: 1,6-nucleophilic addition; CsF/18-crown-6; Me3SiCF2H/Me3SiCF3; difluoromethylation; trifluoromethylation.

Abstract

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